Enterprise Sales Development Representative

Pencil; Chicago, Northern (IL, KY); Hybrid; USD 60,000 - 90,000; Full time

Benefits offered by this job

25 days PTO

Remote-first

Health insurance

Wellness stipend

Parental leave

Flexible hours

Job summary

Pencil, an AI advertising platform, is looking for a Sales Development Representative to drive enterprise and mid-market growth. You will identify and qualify new leads, build pipeline, and schedule meetings and demos for our enterprise and mid-market sales teams.

You’ll generate net-new opportunities starting at $25K ACV and help scale a fast-moving, remote-first organization. Based in the Chicago area, you’ll collaborate with sales/marketing to shape outreach, using LinkedIn Navigator, Apollo,

Qualifications

• Must have 1 year of outbound sales development experience into enterprise accounts.
• Experience in SaaS, tech sales, martech or creative production is preferred.
• Strong communicator who can explain complex ideas clearly in writing and on the phone.
• Consistent, disciplined outbound across calls, email and LinkedIn.
• Comfortable in a fast-moving environment where the playbook is still evolving.
• Proficient with CRM software (e.g., Salesforce) and modern prospecting tools.

Responsibilities

• Lead Generation: Identify and connect with potential clients based on our Ideal Customer Profile. Global coverage with focus on UK and US.
• Lead Nurturing: Keep leads warm with personalized outreach sequences.
• Sales Collaboration: Work with sales to ensure leads are fully qualified and set up for success.
• Tools: Use LinkedIn Sales Navigator, Apollo and Lusha for prospecting; Salesforce to track leads.
• Targets: Hit monthly targets for qualified leads with commissions on qualified leads and closed-won deals.

Skills

Outbound sales

SaaS/tech sales

Communication

Lead generation

Prospecting

Tools

Salesforce

LinkedIn Navigator

Apollo

Lusha

Job description

Some of the world's biggest brands already run their advertising on our AI platform. We're moving fast, want to help us build the pipeline that gets us there?

Due to the location of our client and target customer base, this position requires you to be based in the Chicago, Illinois area . Being locally based is important to support effective prospecting, client engagement, and relationship building within the market.

At Pencil, we've built the operating system for AI-made advertising, the platform that aggregates every major AI model, so creative and marketing teams go from brief to finished asset without stitching tools together themselves. Our mission is to make AI the default in advertising without replacing creative people and we're leading that shift today: running production at scale for some of the world's biggest brands like L'Oréal, Unilever, Bayer, Diageo, and more with the legal, security, and procurement rigor enterprise clients require.
We're backed by The Brandtech Group, a $4B marketing technology company that also owns Oliver and Jellyfish, giving us the scale and reach to work with the world's largest advertisers.

What we're looking for:

Sales Development Representative (SDR) with a genuine enthusiasm for AI, to drive our enterprise and mid-market growth. In this role, you'll identify and qualify new leads, build pipeline, and schedule meetings and demos for our enterprise and mid-market sales teams. You'll play a key role in bringing net-new clients to Pencil, working deals starting at $25K in annual contract value. This role and its process have already been validated and you'll be instrumental in driving a significant share of the opportunities we create.

At Pencil, we believe that great work comes from great people. We foster a culture of collaboration, creativity and continuous learning, where your ideas are valued and your growth is supported. With flexible working from home arrangements, a focus on innovation and a team that celebrates wins together, Pencil is a place where you can make a real impact in a booming industry.

Job Requirements

• Must have 1 year of outbound sales development experience into enterprise accounts, you've navigated large orgs, multi-threaded across stakeholders and know what it takes to get a first meeting with a senior buyer.

• Must have experience in SaaS, tech sales, martech or creative production, or a genuine curiosity about how the world’s biggest brands create and buy their advertising. Our buyers are marketing, procurement and brand leaders, you'll need to speak their language quickly.

• Strong communicator who can explain complex ideas simply and confidently, in writing and on the phone.

• Consistent, disciplined outbound across calls, email and LinkedIn, you treat the pipeline as a numbers game and a craft.

• Comfortable in a fast-moving environment where the playbook is still being written, and happy to help improve it.

• Proficient with CRM software (e.g., Salesforce) and modern prospecting tooling.

Job Responsibilities

• Lead Generation: Identify and connect with potential clients based on our Ideal Customer Profile that’s provided. This role covers global markets, with a focus on the UK and US.

• Lead Nurturing: Keep leads warm and engaged with personalised outreach sequences for those not quite ready to buy, so they're ready when the timing is right.

• Sales Collaboration: Work hand-in-hand with our sales team to make sure every lead is fully qualified against our framework (BANT). You'll help shape the best way to engage each account and set it up for success.

• Tools: Use LinkedIn Sales Navigator, Apollo and Lusha for prospecting and contact data, and Salesforce to track leads, stay organised, and capture what matters.

• Targets: Hit monthly targets for qualified leads. You'll earn commission on qualified leads with additional commission on any that convert to closed-won deals.

Benefits:

• 25 days PTO plus public holidays.

• Remote-first, with access to our offices in The Shard, London and in New York or work anywhere in your home country.

• Health insurance / private medical cover

• Monthly stipend towards wellness, fitness, and learning and development

• Enhanced parental leave policies, whether you become a parent through birth, adoption or surrogacy

• Flexible working hours.